9-Fluorenylmethyl chloroformate supplier

Name
9-Fluorenylmethyl chloroformate
EINECS 249-313-6
CAS No. 28920-43-6
Article Data14
CAS DataBase
Density 1.288 g/cm³
Solubility dioxane: 0.1 g/mL, clear, colorless
Melting Point 62-64 °C(lit.)
Formula C₁₅H₁₁ClO₂
Boiling Point 393.9 °C at 760 mmHg
Molecular Weight 258.704
Flash Point 143.6 °C
Transport Information UN 3261 8/PG 2
Appearance white to off-white powder
Safety 26-36/37/39-45-27
Risk Codes 34-20/21/22
Molecular Structure
Hazard Symbols C,T
Synonyms Formicacid, chloro-, fluoren-9-ylmethyl ester (8CI);Fluorene-9-methanol,chloroformate (8CI);(9H-Fluoren-9-ylmethoxy)carbonyl chloride;9H-Fluoren-9-ylmethyl chloroformate;AminoTag;FMOC chloride;FmocCl;Fmoc-Cl;Carbonochloridic acid,9H-fluoren-9-ylmethyl ester;
PSA 26.30000
LogP 4.17430

Synthetic route

: 32315-10-9
bis(trichloromethyl) carbonate

: 24324-17-2
9-Fluorenylmethanol

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

Conditions

Conditions	Yield
With tributyl-amine In toluene at 0℃; Reagent/catalyst; Solvent; Temperature;	98%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;
With tributyl-amine In toluene at 0℃; for 0.0666667h; Temperature; Flow reactor;	98 %Chromat.
With pyridine In toluene at 0 - 20℃;

: 75-44-5
phosgene

: 24324-17-2
9-Fluorenylmethanol

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

Conditions

Conditions	Yield
In dichloromethane	74%
In dichloromethane
With pyridine In diethyl ether 1.) 1 h, 0 deg C, 2.) 8 h, 25 deg C;
With pyridine In tetrahydrofuran at 0 - 6℃; for 13.5h; Temperature; Large scale;

: 86-73-7
9H-fluorene

nickel-aluminium oxide: nickel-aluminium oxide

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 25 percent 2: 74 percent / CH2Cl2 View Scheme

: 75-44-5
phosgene

F-ether: F-ether

: 24324-17-2
9-Fluorenylmethanol

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

Conditions

Conditions	Yield
In tetrahydrofuran; water	37.9 g (95.8%)

...Expand

: 24324-17-2
9-Fluorenylmethanol

: 503-38-8
trichloromethyl chloroformate

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

Conditions

Conditions	Yield
With dmap In toluene at 20℃; for 24h;

: 115134-37-7
Fmoc-OH

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

Conditions

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide at 83℃; for 2h;

: 67-66-3
chloroform

: 24324-17-2
9-Fluorenylmethanol

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

Conditions

Conditions	Yield
With oxygen In acetonitrile at 20℃; for 3h; Irradiation;

: 632-20-2
D-Threonine

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 157355-81-2
(((9H-fluoren-9-yl)methoxy)carbonyl)-D-threonine

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane	100%

: 1197-55-3
4-aminophenylacetic acid

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: Sodium; [4-(9H-fluoren-9-ylmethoxycarbonylamino)-phenyl]-acetate

Conditions

Conditions	Yield
With sodium carbonate for 16h;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 65577-07-3, 65577-08-4, 67896-52-0
(RS)-1-amino-2-methylpropylphosphinic acid

: 146406-32-8
(1RS)-1-(N-(9-fluorenylmethoxycarbonyl)amino)-2-methylpropylphosphinic acid

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 4℃; for 6h;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 75178-96-0
N-Boc-1,3-diaminopropane

: tert-butyl N-[3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propyl]carbamate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 20℃;	100%
With sodium carbonate In tetrahydrofuran for 12h; Ambient temperature;	92%
With sodium hydrogencarbonate In dichloromethane; water at 20℃;	66%
With sodium hydrogencarbonate In dichloromethane	66%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 175979-08-5
Acetic acid (2S,3S,4R,5S,6R)-3-acetylamino-5-benzyloxy-6-hydroxymethyl-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester

: 175979-09-6
Acetic acid (2S,3S,4R,5S,6R)-3-acetylamino-5-benzyloxy-6-(9H-fluoren-9-ylmethoxycarbonyloxymethyl)-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-4-yl ester

Conditions

Conditions	Yield
With pyridine at 0℃; for 2h;	100%

: 56-91-7
p-aminomethylbenzoic acid

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 164470-64-8
N-(9-fluorenylmethyloxycarbonyl)-4-(aminomethyl)benzoic acid

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water	100%
With sodium carbonate In 1,4-dioxane; water at 20℃; for 12h;	90%
With sodium hydrogencarbonate In 1,4-dioxane at 0℃; for 3h;	68.1%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 672-87-7
L-methyltyrosine

: 246539-83-3
Fmoc-L-(α-Me)Tyr-OH

Conditions

Conditions	Yield
With sodium hydroxide In acetonitrile at 20℃; for 3h; Acylation;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 4299-70-1
L-tryptophan methyl ester

: 147960-24-5
methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tryptophanate

Conditions

Conditions	Yield
	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

Gly-Ala-Phe-NH-Rink-resinEt halide: Gly-Ala-Phe-NH-Rink-resinEt halide

: {1-[(S)-1-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-ethylcarbamoyl]-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions

Conditions	Yield
Multistep reaction;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

Gly-Phe-Ala-NH-Rink-resinEt halide: Gly-Phe-Ala-NH-Rink-resinEt halide

: {1-[(S)-1-((S)-1-Carbamoyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions

Conditions	Yield
Multistep reaction;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 77392-58-6
Paraherquamide

: C43H45N3O7

Conditions

Conditions	Yield
With sodium hydride	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 3646-50-2
3-Amino-3-phenylpropionic acid

: 180181-93-5
(±)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 25h;	100%
With sodium hydroxide In 1,4-dioxane at 20℃; for 4h;	77%
With N-ethyl-N,N-diisopropylamine

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: γ-allyl (2R)-glutamate hydrochloride

: 204251-33-2
γ-allyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate

Conditions

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 20℃; for 4h;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 2-[((2S,3R)-3-Hydroxy-3-methyl-pyrrolidine-2-carbonyl)-amino]-3-methyl-but-2-enoic acid

: 741731-29-3
(2S,3R)-2-(1-Carboxy-2-methyl-propenylcarbamoyl)-3-hydroxy-3-methyl-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane at 20℃; for 23h;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 26177-43-5
3-nitrobenzylamine hydrochloride

: 847834-88-2
(3-nitrobenzyl)carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 618-27-9
hydroxy L-proline

: 189249-10-3
(4S)-Nα-Fmoc-4-hydroxy-L-proline

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃; Inert atmosphere;	100%
With sodium carbonate In 1,4-dioxane; water at 0 - 20℃;	92%
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 9h;

: 868745-08-8
(E)-(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-allylamine

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: [(E)-(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-allyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Conditions

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane at 20℃; for 23h;	100%

: 855419-72-6
C12H15NO2

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 1-(9H-fluorenyl-9-yl)methyl 2-ethyl (2R,3R)-2-methyl-3-phenylaziridine-1,2-dicarboxylate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 25℃; for 20h;	100%

: C13H14N4O4*CF3CO2H

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: C13H14N4O4C15H10O2

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine	100%

: 90243-49-5
methyl (2RS,3SR)-2-amino-3-(1H-indol-3-yl)butanoate

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: methyl (2RS,3SR)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(1H-indol-3-yl)butanoate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 0.166667h;	100%

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 132622-66-3
cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline

: 174148-03-9
(2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane at 20℃; for 5h;	100%
With sodium hydrogencarbonate In 1,4-dioxane; water

: 914606-32-9
[4-(tert-butoxycarbonylamino-methyl)-benzylamino]-acetic acid cyclopentyl ester

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 914606-34-1
[[4-(tert-butoxycarbonylamino-methyl)-benzyl]-(9H-fluoren-9-ylmethoxy-carbonyl)-amino]-acetic acid cyclopentyl ester

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; dichloromethane; water at 0 - 20℃;	100%

: 878158-10-2
(E)-1-(3-(2-aminoethyl)phenyl)-2-(O-methyl hydrocinnam-3’-yl)-ethene

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 878158-11-3
methyl trans-3-{3-[2-[3-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]phenyl]vinyl]phenyl}propionate

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 20℃; for 24h;	100%
With sodium carbonate In 1,4-dioxane at 20℃; for 17h;	82%
With sodium carbonate In 1,4-dioxane; water at 20℃;	3.74 g

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 93779-31-8
benzyl (1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylate

: 1046767-57-0
1-(9H-fluoren-9-yl)methyl 2-benzyl (2S,3aS,6aS)-hexahydro-cyclopenta[b]pyrrole-1,2(2H)-dicarboxylate

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 0 - 20℃;	100%

: 943780-17-4
ethyl 5-(4-aminophenylthio)-4-nitrothiophene-2-carboxylate

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 943780-18-5
ethyl 5-(4-(((9H-fluoren-9-yl)methoxy)carbonylamino)phenylthio)-4-nitrothiophene-2-carboxylate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 18h;	100%

: 1172140-50-9
C9H17NO2

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 1172140-49-6
(3R,3aR,6S,6aR)-(9H-fluoren-9-yl)methyl 3-hydroxy-6-propyltetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate

Conditions

Conditions	Yield
With sodium carbonate In 1,4-dioxane; water at 0℃; for 0.75h; Cooling;	100%
With sodium carbonate In 1,4-dioxane; water at 0℃;

: 1666-13-3
diphenyl diselenide

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 1169497-02-2
O-(9H-fluoren-9-yl)methyl Se-phenyl carbonoselenoate

Conditions

Conditions	Yield
With indium In dichloromethane for 12h; Inert atmosphere; Reflux;	100%
With hydrogenchloride; zinc In water at 20℃; for 0.05h; Ionic liquid; Inert atmosphere;	89%
With zinc at 130℃; for 0.0333333h; Microwave irradiation; Neat (no solvent);	60%
With indium; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 50℃; for 1h; Inert atmosphere;	25%
With caesium carbonate; copper(II) oxide at 80℃; for 1h; Ionic liquid; Inert atmosphere;	90 %Chromat.

: 869201-28-5
allyl 3,6-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 1186302-38-4
allyl 3,6-di-O-benzyl-4-O-9-fluorenylmethyloxycarbonyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	100%

: 1204528-94-8
H-o-Abc2K(Boc)-OCH2COPh

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 1204528-95-9
Fmoc-o-Abc2K(Boc)-OCH2COPh

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 25℃;	100%

: 1109284-47-0
tert-butyl [(1R,2S)-2-amino-6,6-difluorocyclohexyl]carbamate

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 1235545-49-9
tert-butyl 9H-fluoren-9-ylmethyl [(1S,2R)-3,3-difluorocyclohexane-1,2-diyl]biscarbamate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water; acetonitrile for 1.5h;	100%
With sodium hydrogencarbonate In water; acetonitrile for 1.5h;

9-Fluorenylmethyl chloroformate Chemical Properties

IUPAC Name: 9H-Fluoren-9-ylmethyl carbonochloridate
Molecular Formula: C₁₅H₁₁ClO₂
Molecular Weight: 258.70 g/mol
SMILES: C1(c2c(cccc2)c2c1cccc2)COC(=O)Cl
InChI: InChI=1/C15H11ClO2/c16-15(17)18-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14H,9H2
EINECS: 249-313-6
Classification Code: Indicators and reagents; Mutation data
Product Categories: Aromatic Esters; N-Protecting Reagents; Biochemistry; Fluorenes; Fluorenes & Fluorenones; Peptide Synthesis; Protection & Derivatization Reagents (for Synthesis); Protective Reagents (Peptide Synthesis); Synthetic Organic Chemistry; Fmoc-Amino acid series
Index of Refraction: 1.611
Molar Refractivity: 69.74 cm³
Molar Volume: 200.7 cm³
Polarizability: 27.64×10^-24cm³
Surface Tension: 50 dyne/cm
Density: 1.288 g/cm³
Flash Point: 143.6 °C
Enthalpy of Vaporization: 64.38 kJ/mol
Boiling Point: 393.9 °C at 760 mmHg
Melting Point: 62-64 °C(lit.)
Storage temperature: 2-8 °C
Solubility: dioxane: 0.1 g/mL, clear, colorless
Sensitive Moisture Sensitive
Vapour Pressure of 9-Fluorenylmethyl chloroformate (CAS NO.28920-43-6): 2.06E-06 mmHg at 25 °C

9-Fluorenylmethyl chloroformate Uses

9-Fluorenylmethyl chloroformate (CAS NO.28920-43-6) is used for tagging silica-based derivatization reagents in HPLC. It is also used to introduce FMOC group as the FMOC carbamate.

9-Fluorenylmethyl chloroformate Production

As can be expected, this compound may be prepared by reacting 9-fluorenylmethanol with phosgene:

9-Fluorenylmethyl chloroformate Toxicity Data With Reference

mma-sat 100 µg/plate

MUREAV Mutation Research. 170 (1986),23.

9-Fluorenylmethyl chloroformate Safety Profile

Hazard Codes: Corrosive C, Toxic T
Risk Statements: 34-20/21/22
R34:Causes burns.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37/39-45-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S27:Take off immediately all contaminated clothing.
RIDADR: UN 3261 8/PG 2
WGK Germany: 3
RTECS: LQ6250000
F: 10-21
HazardClass: 6.1
PackingGroup of 9-Fluorenylmethyl chloroformate (CAS NO.28920-43-6): II

9-Fluorenylmethyl chloroformate Standards and Recommendations

DOT Classification: 6.1; Label: Poison, Corrosive

9-Fluorenylmethyl chloroformate Specification

9-Fluorenylmethyl chloroformate (CAS NO.28920-43-6), its Synonyms are 1-(9-Fluorenyl)methyl chloroformate ; Carbonochloridic acid, 9H-fluoren-9-ylmethyl ester ; 9H-Fluoren-9-ylmethyl chloroformate ; Fluoren-9-ylmethyl chloroformate ; Formic acid, chloro-, fluoren-9-ylmethyl ester . It is white to off white crystalline powder.

Product Name

9-Fluorenylmethyl chloroformate

Synthetic route

9-Fluorenylmethyl chloroformate Chemical Properties

9-Fluorenylmethyl chloroformate Uses

9-Fluorenylmethyl chloroformate Production

9-Fluorenylmethyl chloroformate Toxicity Data With Reference

9-Fluorenylmethyl chloroformate Safety Profile

9-Fluorenylmethyl chloroformate Standards and Recommendations

9-Fluorenylmethyl chloroformate Specification

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